Why Nobody Cares About Newsletters Anymore

In today's episode Matt and Kolby break down historic media disruptions—from cable TV's ESPN and CNN to Joe Rogan's $250M Spotify deal—pulling out what's working, what's being left on the table, and who actually has a real thesis on AI today, from The Rundown's $10M+ newsletter to HubSpot's media buying spree.Timestamps: 00:00 Intro: AI Anxiety and Plateauing Founders03:59 The Framework: How Founders Should Respond to AI05:14 Is This an AI Bubble? Cable TV's ESPN and CNN Bet08:35 Web 1.0: Huffington Post's $315M Exit and Motley Fool's Billion-Dollar Run09:32 Viral Video Era: BuzzFeed's Rise, Barstool's $551M Sale12:23 Mobile Wave: Industry Dive's $525M Exit14:12 Axios's Smart Brevity and $525M Sale17:27 The Athletic's $500M Sale, Joe Rogan's $250M Deal, and Mr. Beast19:54 The Common Thread: Every Disruptor Needs a Thesis22:40 Who Has a Real AI Thesis Today?24:59 The Rundown AI's $10M+ Newsletter and Its PE Deal29:31 HubSpot's Strategy of Buying Up Media Companies34:55 Local News, AI-Generated Content, and 6AM City46:06 Breaking Points, Ground News, and the Rise of Trusted Filters53:03 Owning a New Category: Latent Space's AI Engineer Events59:13 Every's Bundled AI Tools and Software-Funded Media📌 Resources: The Rundown AIEveryGround NewsLatent SpaceEnjoying the show? Leave a 5-star review on Apple or Spotify, then email [email protected] or [email protected] with a screenshot and a question — we'll answer it on the show.